Trinny Woodall on the Financial Reality of Being Self-Employed

9 to 5ish with theSkimm

theSkimm

Entrepreneurship, Careers, Business

4.7 • 1.9K Ratings

🗓️ 13 August 2025

⏱️ 32 minutes

🔗️ Recording | iTunes | RSS

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Summary

Trinny Woodall went from recovering from addiction in her mid-20s to becoming one of the most beloved authorities in style and fashion. She landed a lucky break with a weekly style column in London, then parlayed her expertise into the TV show What Not to Wear. Life threw her some curveballs, from mourning loved ones to going through 16 rounds of IVF. Today, Trinny gets real about the sacrifices she had to make around those private battles because of her self-employment status. In this episode of 9 to 5ish, Trinny also shares: Why she made herself try a stint in finance Sacrifices she had to make for being self-employed Why she only took three weeks of paid family leave after having her daughter What she learned from having her business fail during the dot com bubble Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	I was in America with my partner who was also pregnant, and we were doing the Oscars with Diana Soya on the red carpet.
0:09.4	I felt this trickle, and I went to the loo, and it was blood, and I thought, fuck, I've lost a baby again.
0:17.2	I'm Carly Zakin, and I'm Danielle Weissberg. Welcome to 9 to 5-ish with the skin. We've run into so many questions over the years and had so many moments where we needed advice and we got it from women who'd been there.
0:32.8	And that's what we're bringing you at this show. Each week we're helping you get what you want out of your career
0:37.7	by talking to the smartest leaders we know. Because we know your work life is a lot more than
0:43.7	nine to five. All right, let's get into it. Hi, everyone. Today's guest is Trinney Woodall. She's the founder and CEO of Trini London,
0:56.9	a beauty brand she launched after building a career in fashion and TV. Trini always gravitated
1:02.7	towards fashion, but before committing to the industry, she tried following in the footsteps of
1:07.3	her dad, testing the waters and finance. She hated it and pivoted to fashion where she
1:13.8	became a well-known London-based style columnist in the 90s. Trinney then ended up hosting a show in the
1:20.5	early 2000s called What Not to Wear, which gained her a loyal following. She launched her company
1:26.3	Trinney London in 2018, which brought stackable,
1:30.0	portable, and premium beauty and skincare to the market. In 2023, Trini published a book and
1:36.2	podcast called Fearless. And if you've ever watched her closet confession series on social media
1:42.0	or been part of the Trini tribe. You already know that she's all
1:46.7	in on helping women feel confident at every age, which we will get into today. Trini, welcome to
1:52.3	9 to 5-ish. Thank you, my dear. Thank you for having me on. We like to do things quickly. So with a
1:58.6	lightning round, quick questions, quick answers. What was the first
2:02.2	job you got paid for? Cutting meat in a delicatess in age 16. Did that make you more or less likely to
2:12.3	eat deli sandwiches? Far less likely. And my pay was docked when I cut the meat too thick.
2:20.7	So I was paid the equivalent of like $25 a day.
2:23.4	And they took $5 off if I cut the meat too thick and it wasn't sellable.
	...

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